苯氧基亚磷酰二氯

苯氧基亚磷酰二氯 基本信息
CAS号 3426-89-9 分子式 C6H5Cl2OP
分子量 194.98300 精确质量  193.94600
PSA  22.82000 LogP  3.76990

基本信息 展开↓

CAS号:
3426-89-9
3D弹球模型:
立即前往扯扯看
分子式:
C6H5Cl2OP
分子量:
194.98300
中文名称:
苯氧基亚磷酰二氯
英文名称:
dichloro(phenoxy)phosphane
中文别名:
苯氧基亚磷酰二氯;
Dichlorophenoxyphosphine Phenoxyphosphorusdichloride Phenyl dichloridophosphite Phenyldichlorophosphite Phosphorodichloridous acid, phenyl ester Phosphorodichloridousacid,phenylester Phenyl phosphorodichloridite Dichloridophosphorous acid phenyl ester
英文别名:
dichloro(phenoxy)phosphane;
phenyl phosphorodichloridate;
PHOSPHORODICHLORIDOUS ACID,PHENYL ESTER;
Phenyl phosphorodichloridite;
Phenyl dichlorophosphite;
EINECS 222-330-6;
diacid chloride of phenyl phosphorous acid;
phosphorodichloridite of phenol;
Phenoxyphosphorus dichloride;
phenyl dichlorophosphinite;
Dichlorophenoxyphosphine;
Phosphorigsaeurephenylesterdichlorid;
Phenyl-phosphorodichloridit
精确分子量/精确质量:
193.94600
极性分子表面积/PSA:
22.82000
油水分配系数/LogP:

LogP值指的是某物质在正辛醇/水两相体系中的分配系数的对数值,反映了物质在油水两相中的分配情况。其中、LogP值越大,说明该物质越亲油;反之,LogP值越小,则说明该物质越亲水。
贝尔斯坦号/MDL:
MFCD00041721
EINECS:
222-330-6
InChI:
The Key: LXHWDUISRBUGRA-UHFFFAOYSA-N

生产制备方法及用途展开↓

制备方法


三氯化磷与苯酚反应可以制备二氯亚磷酸苯酯,但目标产物产率很低。当在反应体系中加入MgCl2并仔细监控反应,可得到高产率产物 (式1)。

合成制备方法


三氯化磷与苯酚反应可以制备二氯亚磷酸苯酯,但目标产物产率很低。当在反应体系中加入MgCl2并仔细监控反应,可得到高产率产物[1]  (式1)。

 

用途简介


二氯亚磷酸苯酯是很好的磷酰化试剂, 用于形成亚磷酸酯、磷酸三酯以及环状有机磷化合物。还适用于高分子合成和酰胺化合物的脱水。合成有机磷化合物二氯亚磷酸苯酯与含有羟基的化合物反应生成亚磷酸三酯 (式2),在氧化试剂氧化下,亚磷酸三酯可以得到磷酸三酯 (式3)。合成有机膦化合物二氯亚磷酸苯酯与醛、胺或酰胺反应可以合成含有P-C键的化合物 (式4)。用于手性有机膦的合成二氯亚磷酸苯酯与手性试剂反应生成手性亚磷酸三酯,它可用作铜催化剂的配体 (式5)。用于合成磷酰胺二氯亚磷酸苯酯与叔丁醇和核苷 (如AZT、d4T) 反应生成核苷亚磷酸二酯,然后在NCS存在下与氨基酸酯反应,可制备核苷磷酰胺,这类化合物具有抗HIV活性,是一类前药 (式6)。

用途


二氯亚磷酸苯酯是很好的磷酰化试剂, 用于形成亚磷酸酯、磷酸三酯以及环状有机磷化合物。还适用于高分子合成和酰胺化合物的脱水。

合成有机磷化合物  二氯亚磷酸苯酯与含有羟基的化合物反应生成亚磷酸三酯 (式2)[2],在氧化试剂氧化下,亚磷酸三酯可以得到磷酸三酯 (式3)[3,4]

合成有机膦化合物  二氯亚磷酸苯酯与醛、胺或酰胺反应可以合成含有P-C键的化合物 (式4)[5]

用于手性有机膦的合成  二氯亚磷酸苯酯与手性试剂反应生成手性亚磷酸三酯,它可用作铜催化剂的配体 (式5)[6]

用于合成磷酰胺  二氯亚磷酸苯酯与叔丁醇和核苷 (如AZT、d4T) 反应生成核苷亚磷酸二酯,然后在NCS存在下与氨基酸酯反应,可制备核苷磷酰胺,这类化合物具有抗HIV活性,是一类前药 (式6)[7]

物化性质展开↓

密度:
1.359
沸点:
99ºC (12 mmHg)
闪点:
87.5ºC
存储条件/存储方法:
库房通风低温干燥,与氧化剂、H发孔剂、氰化物分开存放
稳定性相关:

1.避免与不相容材料,空气,湿空气,水接触。

2.具有刺激性气味,对潮湿敏感。不能和强碱、强氧化剂一起放置。在减压条件下可以重蒸纯化。

其它信息:

1.      性状:无色透明液体

2.      密度(g/mL,25℃):1.359

3.      相对蒸汽密度(g/mL,空气=1):未确定

4.      熔点(ºC):未确定

5.      沸点(ºC,常压):未确定

6.      沸点(ºC,12mmHg):99

7.      折射率(n20/D):未确定

8.      闪点(ºC):未确定

9.      比旋光度(º):未确定

10.   自燃点或引燃温度(ºC):未确定

11.   蒸气压(mPa,20ºC):未确定

12.   饱和蒸气压(kPa,25ºC):未确定

13.   燃烧热(KJ/mol):未确定

14.   临界温度(ºC):未确定

15.   临界压力(KPa):未确定

16.   油水(辛醇/水)分配系数的对数值:未确定

17.   爆炸上限(%,V/V):未确定

18.   爆炸下限(%,V/V):未确定

19.   溶解性:溶于大多数非质子有机溶剂。

安全信息展开↓

海关代码:
2909309090
危险类别码:
34-23-22
安全标志:
S26:万一接触眼睛,立即使用大量清水冲洗并送医诊治。
S28:接触皮肤之后,立即使用大量皂液洗涤。
S38:在通风不良的场所,佩戴合适的呼吸装置。
S45:出现意外或者感到不适,立刻到医生那里寻求帮助(最好带去产品容器标签)。
:
危险标志:
T: Toxic;

合成路线查看所有的合成路线

  • 108-95-2

    苯酚

  • ~68%

  • 3426-89-9

    苯氧基亚磷酰二氯

  • 4894-60-4

    diethyl phenyl phosphite

  • ~66%

  • 589-57-1

    二乙基亚磷酰氯

  • +

  • 3426-89-9

    苯氧基亚磷酰二氯

  • 101-02-0

    亚磷酸三苯酯

  • +

  • 10294-34-5

    三氯化硼

  • 3426-89-9

    苯氧基亚磷酰二氯

  • +

  • 5382-00-3

    diphenyl chlorophosphite

毒理性展开↓

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TD4440000
CHEMICAL NAME :
Phosphorodichloridous acid, phenyl ester
CAS REGISTRY NUMBER :
3426-89-9
BEILSTEIN REFERENCE NO. :
1866404
LAST UPDATED :
199712
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C6-H5-Cl2-O-P
MOLECULAR WEIGHT :
194.98
WISWESSER LINE NOTATION :
GPGOR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#05836
毒理学数据:

1、急性毒性:小鼠经静脉LD50:100mg/kg;

MSDS 展开↓

Name: Phenyl Phosphorodichloridite Material Safety Data Sheet
Synonym: Phosphorodichloridous Acid, Phenyl Ester; Dichlorophenoxyphosphine
CAS: 3426-89-9
Section 1 - Chemical Product   MSDS Name:Phenyl Phosphorodichloridite Material Safety Data Sheet
Synonym:Phosphorodichloridous Acid, Phenyl Ester; Dichlorophenoxyphosphine

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
3426-89-9 Phosphorodichloridous Acid, Phenyl Est ca 100 222-330-6
Hazard Symbols: C
Risk Phrases: 34

Section 3 - HAZARDS IDENTIFICATION
  EMERGENCY OVERVIEW
Causes burns.Corrosive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
May cause severe and permanent damage to the digestive tract. Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
No information found.

Section 4 - FIRST AID MEASURES
  Eyes: Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Destroy contaminated shoes.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:

Section 5 - FIRE FIGHTING MEASURES
  General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

Section 6 - ACCIDENTAL RELEASE MEASURES
  General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

Section 7 - HANDLING and STORAGE
  Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Do not get on skin or in eyes. Avoid ingestion and inhalation. Do not ingest or inhale. Use with adequate ventilation. Discard contaminated shoes.
Storage:
Store in a cool, dry place. Keep container closed when not in use.
Corrosives area.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
  Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 3426-89-9: Personal Protective Equipment Eyes: Wear chemical splash goggles. Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES
 
Physical State: Liquid
Color: clear colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 99 deg C @ 12.00mm Hg
Freezing/Melting Point: 0 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.3590g/cm3
Molecular Formula: C6H5Cl2OP
Molecular Weight: 194.98

Section 10 - STABILITY AND REACTIVITY
  Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Not available.

Section 11 - TOXICOLOGICAL INFORMATION
  RTECS#:
CAS# 3426-89-9: TD4440000 LD50/LC50:
CAS# 3426-89-9: Inhalation, rat: LC50 = >2080 mg/m3/1H; Oral, rat: LD50 = 681 mg/kg.
Carcinogenicity:
Phosphorodichloridous Acid, Phenyl Ester - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION
 

Section 13 - DISPOSAL CONSIDERATIONS
  Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION
 
IATA
Shipping Name: CORROSIVE LIQUID, N.O.S.*
Hazard Class: 8
UN Number: 1760
Packing Group: III
IMO
Shipping Name: CORROSIVE LIQUID, N.O.S.
Hazard Class: 8
UN Number: 1760
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE LIQUID, N.O.S.
Hazard Class: 8
UN Number: 1760
Packing group: III

Section 15 - REGULATORY INFORMATION
 
European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
WGK (Water Danger/Protection)
CAS# 3426-89-9: No information available.
Canada
CAS# 3426-89-9 is listed on Canada's NDSL List.
CAS# 3426-89-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3426-89-9 is listed on the TSCA inventory.


SECTION 16 - ADDITIONAL INFORMATION
N/A

海关数据查看详细

中国海关编码:2909309090

概述:
2909309090 其他芳香醚及其卤化衍生物、磺化、硝化衍生物(包括亚硝化衍生物)。监管条件:无。增值税率:17.0%。退税率:9.0%。最惠国关税:5.5%。普通关税:30.0%
申报要素:
品名, 成分含量, 用途
摘要/Summary:
2909309090 other aromatic ethers and their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

分子结构与计算化学数据展开↓

计算化学数据


1、   疏水参数计算参考值(XlogP):3.4

2、   氢键供体数量:0

3、   氢键受体数量:1

4、   可旋转化学键数量:1

5、   互变异构体数量:2

6、   拓扑分子极性表面积(TPSA):9.2

7、   重原子数量:10

8、   表面电荷:0

9、   复杂度:93.7

10、   同位素原子数量:0

11、   确定原子立构中心数量:0

12、   不确定原子立构中心数量:0

13、   确定化学键立构中心数量:0

14、   不确定化学键立构中心数量:0

15、   共价键单元数量:1

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    三氯化磷

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