Basic information
- CAS
19158-51-1- Standard SMILES
Cc1ccc(S(=O)(=O)C#N)cc1- InChIKey
JONIMGVUGJVFQD-UHFFFAOYSA-N- Molecular formula
- C8H7NO2S
- Average molar mass
- 181.21 g/mol
- Monoisotopic mass
- 181.01974946
Names & identifiers
- Preferred name
- p-Toluenesulphonyl cyanide
- IUPAC
- (4-methylphenyl)sulfonylformonitrile
- English name
- Tosyl cyanide
- Molecular formula
- C8H7NO2S
- Molecular weight
- 181.21
Names & synonyms
19158-51-14-Methylbenzenesulfonyl cyanidep-Toluenesulphonyl cyanideEINECS 242-849-1DTXSID50172685RefChem:858218DTXCID0095176242-849-1Tosyl cyanidep-Toluenesulfonyl cyanide(4-methylphenyl)sulfonylformonitrileBenzenesulfonyl cyanide, 4-methyl-
Show more names
TsCNBenzenesulfonylcyanide, 4-Methyl-Tos-CNosyl cyanidep-Tosyl cyanide
p-Tolylsulfonyl cyanide4-toluenesulfonyl cyanide4-methylbenzene-1-sulfonyl cyanidep-tolylsulfonylformonitrileMFCD00009977p-toluene sulfonyl cyanideTosyl Cyanide (>90%)4-tolylsulfonylcyanide; tosyl cyanide; 4-Methylbenzenesulfonyl cyanide; p-Toluenesulfonyl cyanide;
Database identifiers
- CAS
19158-51-1- PubChem CID
- 87946
- DTXSID
DTXSID50172685- EC Number
- 242-849-1
- Nikkaji
- J224.867K
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 66.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 285
Physicochemical properties
- Melting point
- 47 · 47-50 °C (lit.)
- Boiling point
- 105 · 105-106 °C/1 mmHg (lit.)
- Density
- 1.3055 · 1.3055 (rough estimate)
- refractive index
- 1.565 · 1.5650 (estimate)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Sparingly), Ethyl Acetate
- form
- crystalline solid
- color
- White
- BRN
- 2048159 · 2048159
- Stability
- Hygroscopic, Moisture Sensitive
- InChI
- InChI=1S/C8H7NO2S/c1-7-2-4-8(5-3-7)12(10,11)6-9/h2-5H,1H3
- InChIKey
- JONIMGVUGJVFQD-UHFFFAOYSA-N
- SMILES
- C1(S(C#N)(=O)=O)=CC=C(C)C=C1
- CAS DataBase Reference
- 19158 · 19158-51-1(CAS DataBase Reference)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 312 · H312+H332-H314
- Precautionary statements
- 260 · P260-P271-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C
- Risk Statements
- 20 · 20/21-34
- Safety Statements
- 26 · 26-27-28-36/37/39-45
- RIDADR
- 3261 · UN 3261 8/PG 2
- WGK Germany
- 3 · 3
- F
- 10 · 10-21
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 2930909899 · 2930909899
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationEye Dam. 1Skin Corr. 1B
- Limited Quantities
- 1 Kg · 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P362+P364, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- F
- 10-21
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- ridadr
- UN 3261 8/PG 2
- hs_code
- 2930909899
- risk_code
- 20/21-34
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- C
- safety_code
- 26-27-28-36/37/39-45
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- III
- Hazard statements
- H312+H332-H314
- Limited Quantities
- 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationEye Dam. 1Skin Corr. 1B
- Precautionary statements
- P260-P271-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Applications
Usesp-Toluenesulfonyl cyanide can be used in:The preparation of polyfunctional nitriles.Free-radical cyanation of B-alkylcatecholboranes.The synthesis of 4-hyroxypyridines by hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers.
UsesTosyl cyanide is used in a free-radical cyanation of B-alkylcatecholboranes. Also used as a component in a hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers leading to 4-hyroxypyridines.
General Descriptionp-Toluenesulfonyl cyanide is an electron-deficient nitrile. It undergoes hetero-Diels-Alder reaction with silyl enol ether of cyclohexenone to yield hydrolytically sensitive [4+2] adduct. It also undergoes facile [2+3] cycloaddition reaction with azides to form 5-sulfonyl tetrazoles. p-Toluenesulfonyl cyanide also reacts with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield sulfinates.
Upstream & downstream products
Downstream products
Suppliers100 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
郑州鸿晟医药科技有限公司0371-55695890 15637198702 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]
毕佳索（上海毕得医药科技股份有限公司）400-6005915 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
北京华威锐科化工有限公司0757-86329057 18934348241 · [email protected]
北京索莱宝科技有限公司010-50973130 17801761073 · [email protected]
江苏普乐司生物科技有限公司0513-66017706 18551496367 · [email protected]
上海颖心实验室设备有限公司021-59178156 17002132182 · [email protected]
上海德默医药科技有限公司400-021-7337 2355568890 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
石家庄斯迪亚诺精细化工有限公司0311-89250318 13582355795 · [email protected]
常州科化生物科技有限公司0519-68985668 13685222090 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
医恩医疗系统研发（上海）有限公司021-58958002 18930822973 · [email protected]
Beckmann-Kenko GmbH+49 4241 9308 88 · [email protected]
上海健超生物科技有限公司15021035486 18081542813 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
北京泰亚杰科技有限公司021-33690831-8001 13552411790;18616022633 · [email protected]
河南赢创生物科技有限公司15672878902 · [email protected]
上海汇凯化学科技有限公司021-61995394 18916691159 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
北京环宇世纪化学科技有限公司hysj_bj.com
重庆星灿医药科技有限公司13594048950 19923294409 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
桦特昇生物科技（武汉）有限公司027-59207879 1972026995 18140587686 · [email protected]
江苏倍达医药科技有限公司0512-63009836 18994340901 · [email protected]
无锡仁旺医药有限公司17302505019
上海谱振生物科技有限公司4001650900 13817534909 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
赛诺威（厦门）科技有限公司请加微信(同手机号)或QQ询价 13876246362 · [email protected]
湖北魏氏化学试剂股份有限公司13125137732 18686406941
嘉兴市浙嘉生物科技有限公司0573-85609002 · [email protected]
成都润泽本土化工有限公司028-88469284 18000562381 · [email protected]
成都叮当时代医药科技有限公司028-86040038 · [email protected]
南京艾比克斯生化科技有限公司025-87193546 18652950785 · [email protected]
上海思言生物科技有限公司021-50908862，442785678，326799392 18721037013 · [email protected]
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
Related reactions
76 records
Compound notes
Loading…