Benzyl isocyanate

Base Information

• Chemical Name: Benzyl isocyanate
• CAS No.: 3173-56-6
• Molecular Formula: C8H7NO
• Molecular Weight: 133.15
• Hs Code.: 29291090
• European Community (EC) Number: 221-640-9
• NSC Number: 118415
• UNII: 8I2LI357GQ
• DSSTox Substance ID: DTXSID40863116
• Nikkaji Number: J30.187F
• Wikidata: Q27270562
• Mol file: 3173-56-6.mol

Synonyms:Benzyl isocyanate;3173-56-6;(Isocyanatomethyl)benzene;Benzylisocyanate;Isocyanatomethylbenzene;Isocyanic Acid Benzyl Ester;Benzene, (isocyanatomethyl)-;1-(isocyanatomethyl)benzene;phenylmethyl isocyanate;Benzene, isocyanatomethyl-;UNII-8I2LI357GQ;8I2LI357GQ;EINECS 221-640-9;MFCD00009701;NSC-118415;25550-57-6;benzyl isocynate;phenylmethylisocyanate;NSC118415;Benzyl isocyanate, 99%;(Isocyanatomethyl)benzene #;SCHEMBL5966;DTXSID40863116;GEO-00302;STK504597;AKOS000265473;AM85723;NSC 118415;SB74529;AS-17365;BB 0253728;FT-0604983;I0426;D91149;EN300-108000;J-650077;W-106880;Q27270562;F2163-0007

Chemical Property of Benzyl isocyanate

Chemical Property:

• Appearance/Colour: Clear colourless to faintly yellow liquid
• Vapor Pressure: 0.358mmHg at 25°C
• Melting Point: 259-261 °C(Solv: acetic acid (64-19-7))
• Refractive Index: n20/D 1.526(lit.)
• Boiling Point: 198.5 °C at 760 mmHg
• Flash Point: 45 °C
• PSA: 29.43000
• Density: 0.98 g/cm³
• LogP: 1.52240
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: It hydrolyzes with water.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 133.052763847
• Heavy Atom Count: 10
• Complexity: 132

Purity/Quality:

99% ^*data from raw suppliers

Benzyl isocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T
• Statements: 10-36/37/38-42/43-23/24/25
• Safety Statements: 23-26-36/37-36/37/39-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN=C=O
• Uses: Benzyl isocyanate, is used as a protected ammonia equivalent in the stereo selective ring-opening of chiral 2,3-epoxy alcohols (from Sharpless asymmetric epoxidation). The key step in the sequence involves intramolecular cyclization of the carbamate intermediate. It is also used in a multicomponent, stereospecific synthesis of 1,3-oxazinane-2,4-diones employing an Al-salph complex. Benzyl isocyanate was used to investigate the kinetics of isocyanate derivatization reaction in a continuous flow glass microfluidics chip. It was also used in a multicomponent, stereospecific synthesis of 1,3-oxazinane-2,4-diones employing an Al-salph complex (674699).

Technology Process of Benzyl isocyanate

There total 89 articles about Benzyl isocyanate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

bis(trichloromethyl) carbonate (32315-10-9) + benzylamine (100-46-9) → benzyl isothiocyanate (3173-56-6)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/j.bmc.2013.03.075

Reference yield: 98.0%

carbon dioxide (124-38-9,18923-20-1) + benzyl azide (622-79-7) → benzyl isothiocyanate (3173-56-6)

Guidance literature:

With diphenylphosphinopolystyrene; In acetonitrile; at 50 ℃; for 1.5h; under 10876.1 Torr; Solvent; Pressure; Time; Microwave irradiation;

DOI:10.3762/bjoc.9.274

Reference yield: 84.0%

2-(benzylamino)-2-oxoacetic acid (6345-08-0) → benzyl isothiocyanate (3173-56-6)

Guidance literature:

With ammonium peroxydisulfate; silver nitrate; copper(II) sulfate; In dichloromethane; water; at 40 ℃; for 3h;

DOI:10.1039/c39940000679

upstream raw materials:

phosgene

benzylamine hydrochloride

benzylurea

silver cyanate

Downstream raw materials:

N-(dimethylcarbamoyl)benzylamine

N-phenyl-N'-benzylurea

5-benzylcarbamoyloxy-octan-4-one

1,3-dibenzylurea

Refernces

• 1、 Lam, Tin Yiu,Wang, Yu-Pu,Danheiser, Rick L.. "Benzannulation via the reaction of ynamides and vinylketenes. Application to the synthesis of highly substituted indoles". . p. 9396 - 9414. Retrieved 2013.
• 2、 Addlagatta, Anthony,Ding, Yongzheng,Ma, Chunhua,Marapaka, Anil Kumar,Pillalamarri, Vijaykumar,Reddi, Bharati,Sankoju, Priyanka,Sijwali, Puran Singh,Sudhakar, Renu,Zhang, Guozhen,Zhang, Yingjie. "Development of peptidomimetic hydroxamates as PfA-M1 and PfA-M17 dual inhibitors: Biological evaluation and structural characterization by cocrystallization". supporting information. . Retrieved 2021/12/01.
• 3、 Chen, Jia-Nian,Li, Ting,Cheng, Li,Qin, Tai-Sheng,Sun, Ye-Xiang,Chen, Chu-Ting,He, Yue-Zhen,Liu, Guang,Yao, Di,Wei, Ying,Li, Qiu-Yin,Zhang, Guang-Ji. "Synthesis and in vitro anti-bladder cancer activity evaluation of quinazolinyl-arylurea derivatives". . . Retrieved 2020/09/09.