ChemicalBook > CAS DataBase List > (R)-(-)-Benzyl glycidyl ether

(R)-(-)-Benzyl glycidyl ether

Product Name: (R)-(-)-Benzyl glycidyl ether
CAS No.: 14618-80-5
Chemical Name: (R)-(-)-Benzyl glycidyl ether
Synonyms: tert-butyl 3-oxoazepane-1-carboxylate;azepan-3-one;dicyclopropylmethanamine;tert-butyl 3-hydroxyazepane-1-carboxylate;2-(trimethylsilyl)ethanamine;benzyl piperidin-3-ylcarbamate;(2R)-2-(Benzyloxymethyl)oxirane;benzyl 3-hydroxypiperidine-1-carboxylate;tert-butyl 4-hydroxyazepane-1-carboxylate;5-TMP,2Na
CBNumber: CB9320637
Molecular Formula: C10H12O2
Formula Weight: 164.2
MOL File: 14618-80-5.mol

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(R)-(-)-Benzyl glycidyl ether Property

Melting point:: 88-93°C
Boiling point:: 130 °C (0.1 mmHg)
alpha: -5.4 º (c=5 in toluene)
Density: 1.077 g/mL at 25 °C(lit.)
refractive index: n20/D 1.517(lit.)
Flash point:: >230 °F
storage temp.: 2-8°C
form: paste (yellow)
Specific Gravity: 1.077
color: Colorless to Almost colorless
optical activity: [α]20/D 5.4°, c = 5 in toluene
Water Solubility: Soluble in water.
BRN: 3588399
InChI: InChI=1S/C10H12O2/c1-2-4-9(5-3-1)6-11-7-10-8-12-10/h1-5,10H,6-8H2/t10-/m0/s1
InChIKey: QNYBOILAKBSWFG-JTQLQIEISA-N
SMILES: O1C[C@@H]1COCC1=CC=CC=C1
CAS DataBase Reference: 14618-80-5(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36-37/39
RIDADR: NA 1993 / PGIII
WGK Germany: 3
RTECS: TX2860020
HS Code: 29109000
Toxicity: mic-sat 660 nmol/plate MUREAV 298,197,1993

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 791547
Product name: Titania paste, transparent
Packaging: 10G
Price: $184.07
Updated: 2025/07/31

Sigma-Aldrich

Product number: 791547
Product name: Titania paste, transparent
Packaging: 20G
Price: $337
Updated: 2025/07/31

Sigma-Aldrich

Product number: 720429
Product name: 1H-Pyrazol-3-ylboronic acid hydrate
Packaging: 1g
Price: $251
Updated: 2023/06/20

Sigma-Aldrich

Product number: 363529
Product name: (R)-(?)-Glycidyl benzyl ether
Purity: 99%
Packaging: 1g
Price: $42.4
Updated: 2023/06/20

TCI Chemical

Product number: B2238
Product name: Benzyl (R)-(-)-Glycidyl Ether
Purity: >98.0%(GC)
Packaging: 1g
Price: $20
Updated: 2025/07/31

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(R)-(-)-Benzyl glycidyl ether Chemical Properties,Usage,Production

Chemical Properties

Colorless to light yellow liqui

Uses

Used in the preparation of the lactone fragment of compactin and mevinolin. Chiron in the preparation of syn-1,3-polyols, dideoxynucleosides, and a spiroacetal cyanohydrin.

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 4807, 1980 DOI: 10.1016/0040-4039(80)80145-6

General Description

1H-Pyrazol-3-ylboronic acid hydrate can be used as a reactant in the Suzuki-Miyaura coupling reaction to synthesize pyrazole derivatives by reacting with different aryl halides over the palladium catalyst.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.

Synthesis

100-39-0

60456-23-7

14618-80-5

NaH (179 mg, 4.10 mmol, 55% oil solution) was suspended in THF (2 mL) and cooled to 0 °C under argon protection. A THF solution (4 mL) of (S)-oxiran-2-ylmethanol (S1, 200 mg, 2.70 mmol) and benzyl bromide (0.340 mL, 2.86 mmol) were added sequentially. The reaction mixture was heated and stirred at reflux for 19 hours. After completion of the reaction, the reaction was quenched with 0.1 M phosphate buffer (pH 6.5). The product was extracted with ethyl acetate (3×) and the organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by fast column chromatography on silica gel (eluent: hexane/ethyl acetate = 10/1) to afford (R)-benzyloxymethylepoxane (S21) as a colorless oil (196 mg, 44%).1H NMR (300 MHz, CDCl3) δ = 2.62 (dd, J1 = 2.5 Hz, J2 = 5.0 Hz, 1H), 2.80 (dd, J1 = 3.0 Hz, J2 = 5.0 Hz, 1H), 3.19 (dd, J1 = 2.5 Hz, J2 = J3 = 3.0 Hz, J4 = 5.5 Hz, 1H), 3.44 (dd, J1 = 5.5 Hz, J2 = 11.5 Hz, 1H), 3.77 (dd, J1 = 3.0 Hz, J2 = 11.5 Hz, 1H), 4.57 (d, J = 12.0 Hz, 1H), 4.61 (d, J = 12.0 Hz, 1H), 7.25-7.38 (m, 5H); 13C NMR (75 MHz, CDCl3) δ = 44.3, 50.8, 70.8, 73.3, 127.7, 128.4, 137.8; HRMS (EI) m/z 164.0825 (calculated for C10H12O2, M+ 164.0837).

Purification Methods

This ether in EtOAc is dried (Na2SO4), then purified by flash chromatography using pet ether/EtOAc (5:1) as eluent. The ether distils through a short path distillation apparatus (Kügelrohr) as a colourless liquid. Alternatively, dissolve it in CHCl3, wash it with H2O, dry (Na2SO4), evaporate and purify by silica gel chromatography. [Anisuzzamen & Owen J Chem Soc 1021 1967, Takano et al. Heterocycles 1 6 381 1981, Lipshutz et al. Org Synth 69 82 1990, Takano et al. Synthesis 539 1989, Honda et al. Chem Pharm Bull Jpn 39 1385 1991, Beilstein 12 IV 2277.]

References

[1] Collection of Czechoslovak Chemical Communications, 2009, vol. 74, # 5, p. 651 - 769
[2] Chemistry - A European Journal, 2010, vol. 16, # 47, p. 14074 - 14082
[3] Tetrahedron, 2002, vol. 58, # 25, p. 5109 - 5117
[4] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 2, p. 663 - 677
[5] European Journal of Organic Chemistry, 2005, # 22, p. 4773 - 4788

(R)-(-)-Benzyl glycidyl ether Preparation Products And Raw materials

Raw materials

Sodium hydride (S)-Oxiranemethanol N,N-Dimethylformamide Benzyl bromide Ethyl acetate PETROLEUM ETHER

Preparation Products

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View Lastest Price from (R)-(-)-Benzyl glycidyl ether manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: (R)-(-)-Benzyl glycidyl ether 14618-80-5
Price: US $1.10/g
Min. Order: 1g
Purity: 99.0% min
Supply Ability: 100 tons min
Release date: 2025-09-19

Shaanxi Dideu New Materials Co. Ltd

Product: (R)-(-)-Benzyl glycidyl ether 14618-80-5
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000KGS
Release date: 2025-03-08

Shaanxi Dideu New Materials Co. Ltd

Product: (R)-(-)-Benzyl glycidyl ether 14618-80-5
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98.0%
Supply Ability: 10000KGS
Release date: 2024-11-18

14618-80-5, (R)-(-)-Benzyl glycidyl etherRelated Search:

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