105-81-7

Basic information

• Product Name: 1-Allyl-3-(2-hydroxyethyl)-2-thiourea
• Synonyms: Thiourea,N-(2-hydroxyethyl)-N'-2-propenyl- (9CI);Urea,1-allyl-3-(2-hydroxyethyl)-2-thio- (7CI,8CI);Thiourea,N-(2-hydroxyethyl)-N'-2-propen-1-yl-;1-Allyl-3-(2-hydroxyethyl)thiourea;3-(2-Hydroxyethyl)-1-allyl-2-thiourea;N-(2-Hydroxyethyl)-N'-2-propenylthiourea;N-Allyl-N'-(2-hydroxyethyl)thiourea;N-Allyl-N'-(b-hydroxyethyl)thiourea;NSC 70444
• CAS NO: 105-81-7
• Molecular Formula: C₆H₁₂N₂OS
• Molecular Weight: 160.24
• EINECS: 203-334-7
• Mol File: 105-81-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 76-78 °C(lit.)
• Boiling Point: 259.377 °C at 760 mmHg
• Flash Point: 110.667 °C
• Appearance: white powder
• Density: 1.122 g/cm³
• PKA: 13.50±0.70(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 1-Allyl-3-(2-hydroxyethyl)-2-thiourea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Allyl-3-(2-hydroxyethyl)-2-thiourea(105-81-7)
• EPA Substance Registry System: 1-Allyl-3-(2-hydroxyethyl)-2-thiourea(105-81-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: YR7913000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 105-81-7(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

2-Amino-4-bromothiophenol is used to synthesize benzothiazolylalkylphthalazineacetic acid derivatives. It is also used to prepare 6-?bromo-?2,?3-?disubstituted-?4H-?1,?4-?benzothiazines.

Synthetic route

ethanolamine (141-43-5) + N-allyl isothiocyanate (57-06-7) → 1-allyl-3-(2-hydroxyethyl)-2-thiourea (105-81-7)

Conditions	Yield
With chloroform

1-allyl-3-(2-hydroxyethyl)-2-thiourea (105-81-7) → 2-(allylimino)thiazolidine (13578-59-1)

Conditions	Yield
With hexaethylphosphoric triamide at 160 - 170℃; for 0.583333h;	88.4%
With hydrogenchloride; propylphosphorous acid tetraethyldiamide; acetic anhydride 1.) from 40 to 45 deg C, 30 min, 2.) RT; Yield given. Multistep reaction;

1-allyl-3-(2-hydroxyethyl)-2-thiourea (105-81-7) + diethyl 2-chloro-6-methylpyridine-3,5-dicarboxylate (13602-99-8) → 2-[(Z)-Allylimino]-3-(2-hydroxy-ethyl)-7-methyl-4-oxo-3,4-dihydro-2H-pyrido[3,2-e][1,3]thiazine-6-carboxylic acid ethyl ester (109315-17-5)

Conditions	Yield
In ethanol for 1h; Heating;	35%

1-allyl-3-(2-hydroxyethyl)-2-thiourea (105-81-7) → allyl-(4,5-dihydro-oxazol-2-yl)-amine

Conditions	Yield
With mercury(II) oxide; benzene
With water

1-allyl-3-(2-hydroxyethyl)-2-thiourea (105-81-7) + water (7732-18-5) + HgO → 2-allylimino-oxazolidine

1-allyl-3-(2-hydroxyethyl)-2-thiourea (105-81-7) + 2-benzyl-3-chloro-3-phenyl-2,3-dihydroisoindol-1-one (237769-24-3) → 1-allyl-3-[2-(2-benzyl-3-oxo-1-phenyl-2,3-dihydro-1H-isoindol-1-yloxy)ethyl]thiourea

Conditions	Yield
In tetrahydrofuran at 20℃; for 72h;	0.23 g

1-allyl-3-(2-hydroxyethyl)-2-thiourea (105-81-7) → 3-(2-Acetoxy-ethyl)-2-[(Z)-allylimino]-7-methyl-4-oxo-3,4-dihydro-2H-pyrido[3,2-e][1,3]thiazine-6-carboxylic acid ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 35 percent / ethanol / 1 h / Heating 2: 70 percent / 2 h / Heating View Scheme

1-allyl-3-(2-hydroxyethyl)-2-thiourea (105-81-7) + chloroacetic acid ethyl ester (105-39-5) → (2Z)-2-[(2-hydroxyethyl)imino]-3-allyl-1,3-thiazolidin-4-one

Conditions	Yield
Stage #1: 1-allyl-3-(2-hydroxyethyl)-2-thiourea; chloroacetic acid ethyl ester In propan-1-ol Stage #2: With sodium hydrogencarbonate In ethanol for 0.25h;

1-allyl-3-(2-hydroxyethyl)-2-thiourea (105-81-7) → [Cu2((2Z)-2-[(2-hydroxyethyl)imino]-3-allyl-1,3-thiazolidin-4-one)2Cl2]

Conditions	Yield
Multi-step reaction with 2 steps 1.1: propan-1-ol 1.2: 0.25 h 2.1: acetonitrile / 72 h / Electrochemical reaction View Scheme

Upstream product

• 141-43-5 ethanolamine 
• 57-06-7 N-allyl isothiocyanate